Réaction #9880

Équation de réaction

Lithium

NH3

oct-3-yn-1-ol

t-BuOH

NH3

→

trans-oct-3-en-1-ol

Rendement 95.2%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températuremaintaining the temperature
2. 2
   Autreto evaporate overnight
3. 3
   workup.ADDITIONSaturated NH4Cl solution was added
4. 4
   Extractionthe reaction mixture was extracted with hexane
5. 5
   LavageThe combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively
6. 6
   Autredried
7. 7
   AutreEvaporation of the solvent

Mode opératoire

A solution of oct-3-yn-1-ol (2.52 g, 20.0 mmol), t-BuOH (5 g), THF (10 mL) and liquid NH3 was cooled to −36° C. Pieces of Lithium (0.34 g, 50 mmol) were introduced with vigorous stirrng and maintaining the temperature. After 2 h, NH3 was allowed to evaporate overnight. Saturated NH4Cl solution was added and the reaction mixture was extracted with hexane. The combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively and dried. Evaporation of the solvent gave trans-oct-3-en-1-ol (2.44 g, 95%) as a pale yellow oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.36 (1H, m), 3.66 (2H, t, J=6.3 Hz), 2.25 (2H, m), 2.02 (2H, m), 1.74 (1H, br s), 1.31 (4H, m), 0.88 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.27, 125.78, 62.22, 36.22, 32.59, 31.86, 22.47, 14.20.

Source